N-cyclopropylmethyl-14β-(2-nitrocinnamoylamino)-7,8-dihydronorcodeinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N-cyclopropylmethyl-14β-(2-nitrocinnamoylamino)-7,8-dihydronorcodeinone
• 英文别名: (E)-N-[(4R,4aS,7aR,12bR)-3-(cyclopropylmethyl)-9-methoxy-7-oxo-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-yl]-3-(2-nitrophenyl)prop-2-enamide
• 化学式: C₃₀H₃₁N₃O₆
• 分子量: 529.593
• InChiKey: NISWHUKGCNZDTA-JSZJOHKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-nitrocinnamic acid 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 19.0h， 生成 N-cyclopropylmethyl-14β-(2-nitrocinnamoylamino)-7,8-dihydronorcodeinone
  参考文献：
  名称：

  Structural Determinants of Opioid Activity in Derivatives of 14-Aminomorphinones:  Effect of Substitution in the Aromatic Ring of Cinnamoylaminomorphinones and Codeinones

  摘要：

  In recent years there has been substantial interest in the 14-aminodihydromorphinone derivatives methoclocinnamox (MC-CAM) and clocinnamox (C-CAM). To investigate the importance of the cinnamoyl ring substituent, a series of analogues have been prepared with chloro, methyl, and nitro substituents in the 2' and 4' positions. Despite some discrepancies between the in vitro and in vivo data, a clear SAR could be observed where the 2'-chloro and 2'-methyl ligands consistently displayed higher efficacy than their 4'-substituted analogues. The new series also followed the well-established SAR that 17-methyl ligands have greater efficacy at the A opioid receptor than their 17-cyclopropylmethyl counterparts.

  DOI：

  10.1021/jm0604777

文献信息

• Structural Determinants of Opioid Activity in Derivatives of 14-Aminomorphinones:  Effect of Substitution in the Aromatic Ring of Cinnamoylaminomorphinones and Codeinones
  作者：Nick P. R. Nieland、Humphrey A. Moynihan、Simon Carrington、Jillian Broadbear、James H. Woods、John R. Traynor、Stephen M. Husbands、John W. Lewis

  DOI：10.1021/jm0604777

  日期：2006.8.1

  In recent years there has been substantial interest in the 14-aminodihydromorphinone derivatives methoclocinnamox (MC-CAM) and clocinnamox (C-CAM). To investigate the importance of the cinnamoyl ring substituent, a series of analogues have been prepared with chloro, methyl, and nitro substituents in the 2' and 4' positions. Despite some discrepancies between the in vitro and in vivo data, a clear SAR could be observed where the 2'-chloro and 2'-methyl ligands consistently displayed higher efficacy than their 4'-substituted analogues. The new series also followed the well-established SAR that 17-methyl ligands have greater efficacy at the A opioid receptor than their 17-cyclopropylmethyl counterparts.